As described in Nakano, Preliminary reports of the 48th Annual Meeting of the Society of Polymer Science, Japan (Polymer Preprints, Japan, 48, (7), 1279(1999)), it is known that dibenzofulvene polymerizes and a polymer is obtained. However, in this case, the polymer does not show optical activity, because the polymerization-initiating agent which is not an optically active species is used. On the other hand, as described in “Generalities of Chemistry” No. 18, page 129-136 (1993), it is known that poly(triphenylmethyl methacrylate) shows optical activity. But this polymer has poor solvent-resistance, therefore, it is disadvantageous to use the polymer as an optically active stationary phase for HPLC. As described in Tokkai 2001-106729, an optically active maleimide polymer is already known. This polymer is excellent in solvent-resistance, however, it has disadvantage that its separation ability is poor.
The inventor made a detailed study on giving an optical activity to polymers of the above-mentioned dibenzofulvene or similar compounds thereof which are excellent in solvent-resistance. As a result, it was discovered that when dibenzofulvene or similar compounds thereof are polymerized by using an anionic polymerization initiator having an optically active alkyl group together with a chiral ligand, or when an optically active group-introduced dibenzofulvene or similar compounds thereof are polymerized by using an anion polymerization initiator, the obtained high-molecular-weight compounds show optical activity because main chains of them have a helical structure, which led to the present invention.
It is therefore a first object of this invention to provide a high-molecular-weight compound having excellent solvent resistance and showing optical activity.
It is a second object of this invention to provide an optically active stationary phase applicable to HPLC, having excellent solvent resistance.